Two decades ago, the Hollywood producer Harvey Weinstein invited Ashley Judd to the Peninsula Beverly Hills hotel for what the young actress expected to be a business breakfast meeting. Instead, he had her sent up to his room, where he appeared in a bathrobe and asked if he could give her a massage or she could watch him shower, she recalled in an interview.

“How do I get out of the room as fast as possible without alienating Harvey Weinstein?” Ms. Judd said she remembers thinking.

In 2014, Mr. Weinstein invited Emily Nestor, who had worked just one day as a temporary employee, to the same hotel and made another offer: If she accepted his sexual advances, he would boost her career, according to accounts she provided to colleagues who sent them to Weinstein Company executives. The following year, once again at the Peninsula, a female assistant said Mr. Weinstein badgered her into giving him a massage while he was naked, leaving her “crying and very distraught,” wrote a colleague, Lauren O’Connor, in a searing memo asserting sexual harassment and other misconduct by their boss.

“There is a toxic environment for women at this company,” Ms. O’Connor said in the letter, addressed to several executives at the company run by Mr. Weinstein.

An investigation by The New York Times found previously undisclosed allegations against Mr. Weinstein stretching over nearly three decades, documented through interviews with current and former employees and film industry workers, as well as legal records, emails and internal documents from the businesses he has run, Miramax and the Weinstein Company.

During that time, after being confronted with allegations including sexual harassment and unwanted physical contact, Mr. Weinstein has reached at least eight settlements with women, according to two company officials speaking on the condition of anonymity. Among the recipients, The Times found, were a young assistant in New York in 1990, an actress in 1997, an assistant in London in 1998, an Italian model in 2015 and Ms. O’Connor shortly after, according to records and those familiar with the agreements.

In a statement to The Times on Thursday afternoon, Mr. Weinstein said: “I appreciate the way I’ve behaved with colleagues in the past has caused a lot of pain, and I sincerely apologize for it. Though I’m trying to do better, I know I have a long way to go.”

He added that he was working with therapists and planning to take a leave of absence to “deal with this issue head on.”

Lisa Bloom, a lawyer advising Mr. Weinstein, said in a statement that “he denies many of the accusations as patently false.” In comments to The Times earlier this week, Mr. Weinstein said that many claims in Ms. O’Connor’s memo were “off base” and that they had parted on good terms.

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Some of Mr. Weinstein’s films include, from left to right, “Sex, Lies, and Videotape,” “Pulp Fiction” and “Good Will Hunting.”

He and his representatives declined to comment on any of the settlements, including providing information about who paid them. But Mr. Weinstein said that in addressing employee concerns about workplace issues, “my motto is to keep the peace.”

Ms. Bloom, who has been advising Mr. Weinstein over the last year on gender and power dynamics, called him “an old dinosaur learning new ways.” She said she had “explained to him that due to the power difference between a major studio head like him and most others in the industry, whatever his motives, some of his words and behaviors can be perceived as inappropriate, even intimidating.”

Though Ms. O’Connor had been writing only about a two-year period, her memo echoed other women’s complaints. Mr. Weinstein required her to have casting discussions with aspiring actresses after they had private appointments in his hotel room, she said, her description matching those of other former employees. She suspected that she and other female Weinstein employees, she wrote, were being used to facilitate liaisons with “vulnerable women who hope he will get them work.”

The allegations piled up even as Mr. Weinstein helped define popular culture. He has collected six best-picture Oscars and turned out a number of touchstones, from the films “Sex, Lies, and Videotape,” “Pulp Fiction” and “Good Will Hunting” to the television show “Project Runway.” In public, he presents himself as a liberal lion, a champion of women and a winner of not just artistic but humanitarian awards.

In 2015, the year Ms. O’Connor wrote her memo, his company distributed “The Hunting Ground,” a documentary about campus sexual assault. A longtime Democratic donor, he hosted a fund-raiser for Hillary Clinton in his Manhattan home last year. He employed Malia Obama, the oldest daughter of former President Barack Obama, as an intern this year, and recently helped endow a faculty chair at Rutgers University in Gloria Steinem’s name. During the Sundance Film Festival in January, when Park City, Utah, held its version of nationwide women’s marches, Mr. Weinstein joined the parade.

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Harvey Weinstein and Hillary Clinton in 2012. Mr. Weinstein held a fund-raiser for Mrs. Clinton at his Manhattan home last year.CreditLarry Busacca/Getty Images

“From the outside, it seemed golden — the Oscars, the success, the remarkable cultural impact,” said Mark Gill, former president of Miramax Los Angeles when the company was owned by Disney. “But behind the scenes, it was a mess, and this was the biggest mess of all,” he added, referring to Mr. Weinstein’s treatment of women.

Dozens of Mr. Weinstein’s former and current employees, from assistants to top executives, said they knew of inappropriate conduct while they worked for him. Only a handful said they ever confronted him.

Mr. Weinstein enforced a code of silence; employees of the Weinstein Company have contracts saying they will not criticize it or its leaders in a way that could harm its “business reputation” or “any employee’s personal reputation,” a recent document shows. And most of the women accepting payouts agreed to confidentiality clauses prohibiting them from speaking about the deals or the events that led to them.

Charles Harder, a lawyer representing Mr. Weinstein, said it was not unusual to enter into settlements to avoid lengthy and costly litigation. He added, “It’s not evidence of anything.”

At Fox News, where the conservative icons Roger E. Ailes and Bill O’Reilly were accused of harassment, women have received payouts well into the millions of dollars. But most of the women involved in the Weinstein agreements collected between roughly $80,000 and $150,000, according to people familiar with the negotiations.

In the wake of Ms. O’Connor’s 2015 memo, some Weinstein Company board members and executives, including Mr. Weinstein’s brother and longtime partner, Bob, 62, were alarmed about the allegations, according to several people who spoke on the condition of anonymity. In the end, though, board members were assured there was no need to investigate. After reaching a settlement with Mr. Weinstein, Ms. O’Connor withdrew her complaint and thanked him for the career opportunity he had given her.

“The parties made peace very quickly,” Ms. Bloom said.

Through her lawyer, Nicole Page, Ms. O’Connor declined to be interviewed. In the memo, she explained how unnerved she was by what she witnessed or encountered while a literary scout and production executive at the company. “I am just starting out in my career, and have been and remain fearful about speaking up,” Ms. O’Connor wrote. “But remaining silent is causing me great distress.”

In speaking out about her hotel episode, Ms. Judd said in a recent interview, “Women have been talking about Harvey amongst ourselves for a long time, and it’s simply beyond time to have the conversation publicly.”

A Common Narrative

Ms. Nestor, a law and business school student, accepted Mr. Weinstein’s breakfast invitation at the Peninsula because she did not want to miss an opportunity, she later told colleagues. After she arrived, he offered to help her career while boasting about a series of famous actresses he claimed to have slept with, according to accounts that colleagues compiled after hearing her story and then sent on to company executives.

“She said he was very persistent and focused though she kept saying no for over an hour,” one internal document said. Ms. Nestor, who declined to comment for this article, refused his bargain, the records noted. “She was disappointed that he met with her and did not seem to be interested in her résumé or skill set.” The young woman chose not to report the episode to human resources personnel, but the allegations came to management’s attention through other employees.

Across the years and continents, accounts of Mr. Weinstein’s conduct share a common narrative: Women reported to a hotel for what they thought were work reasons, only to discover that Mr. Weinstein, who has been married for most of three decades, sometimes seemed to have different interests. His home base was New York, but his rolling headquarters were luxury hotels: the Peninsula Beverly Hills and the Savoy in London, the Hôtel du Cap-Eden-Roc near the Cannes Film Festival in France and the Stein Eriksen Lodge near the Sundance Film Festival.

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The Peninsula Beverly Hills, a hotel where Mr. Weinstein has been accused of sexually harassing women in the entertainment industry.CreditFG/Bauer-Griffin, via Getty Images

Working for Mr. Weinstein could mean getting him out of bed in the morning and doing “turndown duty” late at night, preparing him for sleep. Like the colleague cited in Ms. O’Connor’s memo, some junior employees required to perform those tasks said they were disturbing.

In interviews, eight women described varying behavior by Mr. Weinstein: appearing nearly or fully naked in front of them, requiring them to be present while he bathed or repeatedly asking for a massage or initiating one himself. The women, typically in their early or middle 20s and hoping to get a toehold in the film industry, said he could switch course quickly — meetings and clipboards one moment, intimate comments the next. One woman advised a peer to wear a parka when summoned for duty as a layer of protection against unwelcome advances.

Laura Madden, a former employee who said Mr. Weinstein prodded her for massages at hotels in Dublin and London beginning in 1991, said he had a way of making anyone who objected feel like an outlier. “It was so manipulative,” she said in an interview. “You constantly question yourself — am I the one who is the problem?”

Most women who told The Times that they experienced misconduct by Mr. Weinstein had never met one another. They range in age from early 20s to late 40s and live in different cities. Some said they did not report the behavior because there were no witnesses and they feared retaliation by Mr. Weinstein. Others said they felt embarrassed. But most confided in co-workers.

Ms. Madden later told Karen Katz, a friend and colleague in the acquisitions department, about Mr. Weinstein’s overtures, including a time she locked herself in the bathroom of his hotel room, sobbing. “We were so young at the time,” said Ms. Katz, now a documentary filmmaker. “We did not understand how wrong it was or how Laura should deal with it.”

Others in the London office said the same. “I was pretty disturbed and angry,” said Sallie Hodges, another former employee, recalling the accounts she heard from colleagues. “That’s kind of the way things were.”

The human resources operation was considered weak in New York and worse in London, so some employees banded together in solidarity. “If a female executive was asked to go to a meeting solo, she and a colleague would generally double up” so as not to be alone with Mr. Weinstein, recalled Mr. Gill, the former president of Miramax Los Angeles.

Many women who worked with Mr. Weinstein said they never experienced sexual harassment or knew of anyone who did, and recalled him as a boss who gave them valuable opportunities at young ages. Some described long and satisfying careers with him, praising him as a mentor and advocate.

But in interviews, some of the former employees who said they had troubling experiences with Mr. Weinstein asked a common question: How could allegations repeating the same pattern — young women, a powerful male producer, even some of the same hotels — have accumulated for almost three decades?

“It wasn’t a secret to the inner circle,” said Kathy DeClesis, Bob Weinstein’s assistant in the early 1990s. She supervised a young woman who left the company abruptly after an encounter with Harvey Weinstein and who later received a settlement, according to several former employees.

Speaking up could have been costly. A job with Mr. Weinstein was a privileged perch at the nexus of money, fame and art, and plenty of his former assistants have risen high in Hollywood. He could be charming and generous: gift baskets, flowers, personal or career help and cash. At the Cannes Film Festival, according to several former colleagues, he sometimes handed out thousands of dollars as impromptu bonuses.

Mr. Weinstein was a volcanic personality, though, given to fits of rage and personal lashings of male and female employees alike. When a female guest of his had to wait for a hotel room upgrade, he yelled that Ms. O’Connor would be better off marrying a “fat, rich Jewish” man because she was probably just good for “being a wife” and “making babies,” she wrote in her memo. (He added some expletives, she said.) His treatment of women was sometimes written off as just another form of toxicity, according to multiple former employees.

In the fall of 1998, a 25-year-old London assistant named Zelda Perkins confronted Mr. Weinstein. According to former colleagues, she and several co-workers had been regularly subjected to inappropriate requests or comments in hotel rooms, and she was particularly concerned about the treatment of another woman in the office. She told Mr. Weinstein that he had to stop, according to the former colleagues, and that she would go public or initiate legal action unless he changed his behavior.

Steve Hutensky, one of Miramax’s entertainment lawyers, was dispatched to London to negotiate a settlement with Ms. Perkins and her lawyer. He declined to comment for this article.

Ms. Perkins, now a theater producer in London, also declined to comment for this article, saying that she could not discuss her work at Miramax or whether she had entered into any agreements.

Months after the settlement, Mr. Weinstein triumphed at the Oscars, with “Life Is Beautiful” and “Shakespeare in Love” winning 10 awards. A few years later, Mr. Weinstein, who had produced a series of British-themed movies, was made a Commander of the British Empire, an honorary title just short of knighthood.

‘Coercive Bargaining’

For actors, a meeting with Mr. Weinstein could yield dazzling rewards: scripts, parts, award campaigns, magazine coverage, influence on lucrative endorsement deals. He knew how to blast small films to box office success, and deliver polished dramas like “The King’s Speech” and popular attractions like the “Scary Movie” franchise. Mr. Weinstein’s films helped define femininity, sex and romance, from Catherine Zeta-Jones in “Chicago” to Jennifer Lawrence in “Silver Linings Playbook.”

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The actress Ashley Judd in the 1997 film “Kiss the Girls.” Ms. Judd said that Mr. Weinstein sexually harassed her two decades ago in his room at the Peninsula.CreditParamount Pictures, via Photofest

But movies were also his private leverage. When Mr. Weinstein invited Ms. Judd to breakfast in Beverly Hills, she had been shooting the thriller “Kiss the Girls” all night, but the meeting seemed too important to miss. After arriving at the hotel lobby, she was surprised to learn that they would be talking in his suite; she decided to order cereal, she said, so the food would come quickly and she could leave.

Mr. Weinstein soon issued invitation after invitation, she said. Could he give her a massage? When she refused, he suggested a shoulder rub. She rejected that too, she recalled. He steered her toward a closet, asking her to help pick out his clothing for the day, and then toward the bathroom. Would she watch him take a shower? she remembered him saying.

“I said no, a lot of ways, a lot of times, and he always came back at me with some new ask,” Ms. Judd said. “It was all this bargaining, this coercive bargaining.”

To get out of the room, she said, she quipped that if Mr. Weinstein wanted to touch her, she would first have to win an Oscar in one of his movies. She recalled feeling “panicky, trapped,” she said in the interview. “There’s a lot on the line, the cachet that came with Miramax.”

Not long afterward, she related what had happened to her mother, the singer Naomi Judd, who confirmed their conversation to a Times reporter. Years later, Ashley Judd appeared in two Weinstein films without incident, she said. In 2015, she shared an account of the episode in the hotel room with “Variety” without naming the man involved.

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In 1997, Mr. Weinstein reached a settlement with the actor Rose McGowan after an episode in a hotel room during the Sundance Film Festival. She had just appeared in the movie “Scream,” above.CreditDimension Films, via Photofest

In 1997, Mr. Weinstein reached a previously undisclosed settlement with Rose McGowan, then a 23-year-old-actress, after an episode in a hotel room during the Sundance Film Festival. The $100,000 settlement was “not to be construed as an admission” by Mr. Weinstein, but intended to “avoid litigation and buy peace,” according to the legal document, which was reviewed by The Times. Ms. McGowan had just appeared in the slasher film “Scream” and would later star in the television show “Charmed.” She declined to comment.

Increased Scrutiny

Just months before Ms. O’Connor wrote her memo, a young female employee quit after complaining of being forced to arrange what she believed to be assignations for Mr. Weinstein, according to two people familiar with her departure. The woman, who asked not to be identified to protect her privacy, said a nondisclosure agreement prevented her from commenting.

Soon, complaints about Mr. Weinstein’s behavior prompted the board of his company to take notice.

In March 2015, Mr. Weinstein had invited Ambra Battilana, an Italian model and aspiring actress, to his TriBeCa office on a Friday evening to discuss her career. Within hours, she called the police. Ms. Battilana told them that Mr. Weinstein had grabbed her breasts after asking if they were real and put his hands up her skirt, the police report says.

The claims were taken up by the New York Police Department’s Special Victims Squad and splashed across the pages of tabloids, along with reports that the woman had worked with investigators to secretly record a confession from Mr. Weinstein. The Manhattan district attorney’s office later declined to bring charges.

But Mr. Weinstein made a payment to Ms. Battilana, according to people familiar with the settlement, speaking on the condition of anonymity about the confidential agreement.

The public nature of the episode concerned some executives and board members of the Weinstein Company. (Harvey and Bob Weinstein together own 42 percent of the privately held business.) When several board members pressed Mr. Weinstein about it, he insisted that the woman had set him up, colleagues recalled.

Ms. Battilana had testified in court proceedings against associates of former Prime Minister Silvio Berlusconi of Italy who are accused of procuring women for alleged sex parties, and the Italian news media also reported that, years ago, Ms. Battilana accused a septuagenarian boyfriend of sexual harassment, a complaint that was apparently dismissed. Ms. Battilana did not respond to requests for comment. Her lawyer, Mauro Rufini, could not be reached for comment.

After the episode, Lance Maerov, a board member, said he successfully pushed for a code of behavior for the company that included detailed language about sexual harassment.

Then Ms. O’Connor’s memo hit, with page after page of detailed accusations. In describing the experiences of women at the company, including her own, she wrote, “The balance of power is me: 0, Harvey Weinstein: 10.”

She was a valued employee — Mr. Weinstein described her as “fantastic,” “a great person,” “a brilliant executive” — so the complaint rattled top executives, including Bob Weinstein. When the board was notified of it by email, Mr. Maerov insisted that an outside lawyer determine whether the allegations were true, he said in an interview.

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Mr. Weinstein in 1999 with the winners of the best-picture Oscar for “Shakespeare in Love.”CreditHector Mata/Agence France—Presse

But the inquiry never happened. Mr. Weinstein had reached a settlement with Ms. O’Connor, and there was no longer anything to investigate.

“Because this matter has been resolved and no further action is required, I withdraw my complaint,” Ms. O’Connor wrote in an email to the head of human resources six days after sending her memo. She also wrote a letter to Mr. Weinstein thanking him for the opportunity to learn about the entertainment industry.